Episode 17: Building your #MSP Employee Onboarding

In this live webcast, Alex and Speaker A walk MSP owners through a practical, repeatable employee‑onboarding framework. They start by stressing the importance of hiring for cultural fit and discuss where talent can be sourced (referrals, retail, tech schools, etc.). They then map the pre‑hire “day‑zero” tasks – HR paperwork, laptop provisioning, welcome swag, and account creation – and outline the first‑day experience. The bulk of the session is a collaborative “bad‑idea” brainstorming that surfaces the many onboarding components: compliance paperwork, PSA/CRM training, shadowing, communication policies, payroll/PTO education, cybersecurity awareness, and product/service catalog familiarisation. They stress breaking training into bite‑size chunks over 60‑90 days, using mentors, check‑ins, and quarterly employee QBRs to reinforce learning, accountability, and career path planning. A cheat‑sheet and worksheet are promised for attendees, and a follow‑up session on sales‑commission planning is announced. The hosts also promote RejectionCon, a pay‑what‑you‑can MSP conference supporting the Rural Tech Fund.
Chapters
What's up?
Wouldn't be a webcast if we didn't start with something on mute.
Uh, you know, well, eventually we'll do an after-hours episode, and I think we should just turn it into a drinking game.
You think I say too much now? Imagine what comes out when I'm properly lubricated.
Ooh, that would actually be kind of fun. And we'll just, we'll just turn it into griping and we'll just be the shit that annoys us. Anywho, thank you everybody for hopping on.
Properly caffeinated.
Yeah, that's where I screwed up with, you know, old water.
Yeah, so thank you for joining us for a half properly caffeinated webcast.
Oh yes, exactly, exactly. And it's actually a fun topic because, Alex, I think we got, you know, as a, as a, for everyone that's watching, we recognize that Sometimes our episodes don't have prescriptions, and that can kind of be frustrating, right? When we don't know, hey, what's the next step? These guys talked very esoterically. I agree with what they're saying, but what do I do?
Yeah.
And right, you and I talked as operators. I want to know what I do. So we're going to get a little bit back to basics today. And what are we doing?
Yeah, yeah. So we're going to dive in and kind of continue the conversation that we had in our, in our breakout session. IT Nation, which was a fantastic breakout. We got some really good feedback on it. I actually did a LinkedIn post on this. Like, not only did we get some, some confirmation that what we're building at Empath is headed in the right direction and that we're building the right thing, we also had some guys come and challenge us and say, hey, you know, I hear what you're saying, but, but there's more. Like, this is a big journey, and don't forget about— and they left us some good little tidbits. So I'll keep all the details out of it, but I think that there's real opportunity here., for us to dig in deep. And, and we'll get into some of that today as we talk through what a proper employee onboarding looks like, right? We hired that new person and how do we make them efficient?
Yeah, completely. And beyond that, for everyone that is attending today that's in Crowdcast, and this is the only place that we're going to post the URL on this one, we actually built you guys a little cheat sheet, um, that we're going to post at the end of the, the session to where you'll actually be able to take everything we talk about today because there's a lot that your employees need to develop as they grow and mature in your organization, uh, that you can use in your own MSPs. And this comes from a lot of what Alex, myself, a lot of the MSPs we've been interacting with. And if you guys interact a lot today as well, we'll go and modify this document and put those in here. So we're going to do some whiteboarding today. Um, on that, just so you guys know, uh, next— or our next session, actually— oops, too many button presses. Uh, we're going to get into building your sales commission plan. Um, we've had a lot of conversation about this. We've had a lot of people ask for this. I even did a session at NextGen back in October on this very topic, and we're going to bring possibly one of the best guys that knows this whole conversation, Adam Slutskin. So that's December 19th, 1 Eastern. Um, we'll make sure in our newsletter, by the way, we're going to change it up to where it's going to give you some ICS files to hold people accountable to the attendance. So keep an eye out on the newsletter. They're still going to come for K7 Leadership for just a little bit longer as we figure out email marketing, but you guys understand that hustle.
Yep, yep. And I will say, as somebody who thinks they have their sales game dialed in, um, Adam's commission plan conversation is way deeper and honestly adds some, some real sane logic to things that I always thought I had figured out. And he definitely had me even scratching my head a little bit and going, oh, I hadn't thought about that. So If you think you've got your sales guy's commission plan figured out, definitely show up and we'll enjoy the conversation on exactly how to build this right and not back yourself into a corner by offering unlimited commissions to a guy who, you know, you want him to earn. You don't want him to stop selling on the 15th when they hit their quota, right? So great conversations to be had here.
Right on. So in that, right, our agenda today, right, we're going to talk a little bit about the framework. Who is the new hire we're bringing on board? This is an important thing to distinguish because your, your onboarding plan. While it's going to be very similar for most people on your team, there are going to be some ways where that deviates. Uh, we're going to talk about, right, where should your new hires start? This is going to be collaborative, right? I want a lot of your guys' input on where we're going to start this journey. We're going to start to build out what this project plan looks like. Uh, practical steps for creating engagement. We're gonna do a little facilitation here, so we're gonna have a little bit of wordplay on where are all the things. Let's do a bad idea session. What are all the things we think we need to add to an onboarding Plan, because I would like to hear from you guys. You might have some things that we've never thought of. Uh, leveraging technology and human resources, right? Where do we sometimes have some stopgaps in what we learn, um, and what we assign our team? I know for the longest time I didn't think to talk to my new hires about what we sell, and that became a massive stopgap down the road. And then some real-world examples. So with that being said, talk to us about Reed, Alex.
Yes, so this is a great conversation just about the culture that gets brought up as we start to have conversations around when we introduce somebody new to the organization. One, how does it change the organization? But two, are we hiring the right people and are we bringing right— the right people in who support the cultures that we have? I hired some really, really smart people at my MSP who absolutely crashed and burned because we had a very specific culture. We had a very tough culture at my MSP. There was a tough love culture there. And the guys who flourished in that environment did really, really well. And the folks who didn't, it was a tough place for them. And a lot of them didn't last very long. So not something I'm proud of. We were, we were not real good at hiring the right fit and the right people. And that's kind of what we wanted to start the conversation with today is getting the right person into your culture. Will not only allow them to perform better, but it'll mean they stick around longer. Right? It means, it means that you have employee retention almost baked in because the right person feels like they go to work with a mission on the same page as the rest of the team. And the wrong person dreads coming to work and is looking for something else to do almost from day one.
Well, and, and I think, Alex, this is probably a good way to start with who are our new hires, right? Like, who are these people that are starting to work for our MSP?
And well, I only hired mine from Facebook and Google. How about you?
If we talk about where we got mine from, I might get, you know, chased out of town because I would find money from—
well, I was just gonna say, I think it's important to point out though, like, we're not hiring from Facebook, right? Where, where were you? Where did you get yours from?
So it depends on the person. Restaurants. I, I'd get them from hotels. I'd I'm commonly quoted with, I'd get a lot of my employees from Nordstrom's because I just walk into a Nordstrom's, put my feet on the carpet with a timer and go, whoever contacts me first, they're my account manager. Because I recognize that it's more about speed to iterative improvement than it is speed to a unicorn, right? A lot of us think that we're going for unicorns in this channel and it's not the case.
And I think as a good refresher, I was in Delaware and we didn't have a Nordstrom's. We weren't that fancy. So, you know, we ended up, we ended up doing some different things, right? I hired a mason at one point who just happened to be a video gamer that really enjoyed technology and wanted to learn newer and better things. And he fit that tough, tough love culture. And he didn't mind getting, you know, that he didn't mind that the culture that we had and actually he flourished in it. And, you know, 8 years later was my service manager. So it's interesting just as we kind of figure out The reason we turned today into a worksheet, I think this kind of plays into it, is that no two of you are going to do this the same. No two of you have the same experience to this point. So make sure that as you're working your way through the worksheet, you take in mind you need to customize this and make it your own. Just taking Alex and Kyle's stuff and stealing it will not give you the desired result.
No, it won't.
Between the two of us, we're very different.
Well, and this is where frameworks are great, but frameworks do not get you to the, the end goal or the be-all of your MSP. Um, and I— we had a great guest on about a few months ago now, right? Peter Kajawa. And I think this kind of sets the tone for the, the talent factory verbiage we've been using, which is MSPs, in their mind, we think that we're NFL teams, but what we actually are is we're college-level football teams. We have to be ready to have a player at full capacity playing in games and also recognize that that development may only last 4 years, right? We may only get 4 good years out of our employees because, right, our enterprise is going to completely steal it from us. We will never be able to afford— I don't care how many benefits you stack for them. I want them to make $200 grand a year. Am I going to pay them that? No. I just— our mechanism as an as-a-service provider does not allow for that type of cost. The numbers don't allow it. So how do we get someone from zero to a hero and start a full career where they're providing or they become their own entrepreneurs? Right. There's this whole journey that you can look at this from. So as we start to, to unpack this, right, I think who we are hiring is somebody that's completely green. They don't know nothing.
Typically, that was the reality for us, right? We had a great relationship with a local VoTech school and we were hiring guys who had just finished their A+ and their Net+. And wanted to get into the technology industry, and this was their first stop. And they would work for me for 3, 4, 5 years, and then the state of Delaware would come poach them right out of my building. And no matter how good a benefits package we stacked up, we couldn't compete with the state.
No. And like Vince mentioned, right, referrals from people I know in the industry, that has a limitation. When you get to a point where you're hiring 2, 3 people a month because you're really trying to scale, you, you can't sit there and have your hiring cycles be 6 months 7 months, 9 months, right? I know an MSP right now, they've been trying to spend 6 months finding a service manager. What's been happening to their service while they've waited for this journey? Things have started to splinter. People aren't following up. Employees are getting away with things, right? They're now conditioning themselves to a little less accountability.
And, and that, that plays into culture, right? That will stick around for a long time, even if they— after they hire a new service manager. It's not like we just flip the switch. And that goes back to where it was.
No, the worst thing you can do is let them start developing a bad habit and then slap their hands 3 months down the road and say, stop doing that. They're like, dude, you've let me get away with it for 3 months, what's changed?
Yep.
So what we have to do is start putting together, right, that roadmap to— I don't care who I'm hiring, right? And this is where you'll see a lot of really successful MSPs talk about, I can train hard skills, I can't train soft skills, right? So When I'm recruiting and when I'm hiring, I'm really looking for those core values, right? What can I work with? Where are their conversations? Where are their soft skills? Everything else, as long as they're willing, eager, and ready to go, let's get started.
When I coached volleyball, we always said you can't teach tall, right? And there are certain soft skills that you want your people to have when they start with you that are just uncoachable. Um, to the exact opposite of that, uh, my mentor in the space was brilliant guy who you wouldn't dare put in front of a customer. And I spent, uh, you know, plenty an hour, um, you know, standing between him and a customer while he fixed something that was really complicated that was beyond my skill set, and not letting him talk to a human and just playing English to English translator. And that's a terrible way to do business too. We have to find that happy place where we, we can hire for soft skill and train up to the, to the level that we really want that person to be at in their technical skills.
Completely right. And that's where Once we do find that individual, right, that first step of we're made, we made the offer, they're ready to go. The last thing we want to do is not have an air of confidence that they made the right decision, especially when they are going to probably take a little bit of a leap of faith on you. Because if it's at the beginning of their career or it's a career change, right, they're going to have a lot of anxiety. They're going to have a lot of stress. They're going to have a lot of unknown of, did I make the right decision? Will I be successful? Or is my my mortgage or my rent at jeopardy, right? Like, I have to be able to give them the, hey, here's how we are going to get you going, right? So that very positive first impression that you can give them is on day 1, you roll out the red carpet and say, here's the next 60 to 90 days of your employment. Here's everything you are going to learn. Here are all of the expectations. You will not be accountable. You are just a sponge. And by the way, you're going to forget half of the stuff that I teach you. And I used to tell my, my new employees this all the time. I expect you to forget 80% of what we teach over the first 60 days. I just want it to be familiar. I want you to have the opportunity and then we will go ahead and mentor you, right? That second step of learning into what we, the behaviors and KPIs that we want to see.
I think this only gets more important as we look at the younger generations that are coming up, right? They're, they're way more about culture. Than they are about any other part of work. Um, so it's really important that on day one, as they walk in the door, we let them understand we have a culture of clear expectations, and we're going to put our expectation out there in front of you. We're expect you to live up to it. Um, if we get there early, it's the same as that employee who we let act up for 3 months and then go slap their hand, right? If we get there early and set the expectation, we're going to wind up with a better, happier employee for the long run. But it's not easy, right? These kids have a Um, it's just a different culture than, than the old fogies like me who, uh, you know, just, uh, I remember in my early jobs, you know, bosses just yelling at you if stuff didn't get done. It's not the world we live in today. Um, so we've got to make sure we set that expectation up front and that we guide these younger, younger folks towards the direction we want them to go. So what does that really look like, right?
Exactly. And being just a comment on that, we can't be the grumpy old men that just think we're going to muscle the next generation into our ways. It's not going to get you very far. And honestly, in the late— I don't know if you notice this at all in your MSP, Alex. With mine, I would notice differentiation just between my employees, the ones in their 30s, the ones in their 40s, and the ones coming in in their 20s. So you end up having multiple generations that you have to balance. So you kind of have to take the least common or most common denominator, whichever way you perceive it, of how your standards get created. Yeah, right. I'd rather be overnurturing to somebody that's like, dude, just let me get going, and have them give me that feedback of, dude, can I just get going, rather than assume that they don't want that.
So I think it's all the same thing.
I, I think this might be a good place to kind of start some whiteboarding, Alex. What do you think?
Let's do it.
Because I, I'm thinking that, and as you know, as you guys know, we're kind of doing this with you all, um there is a layer. Let me get it going to where we're kind of starting to build out a workflow, right? Which is, right, first we need to identify the person, the individual, right? We need to find them. This is recruitment. Um, and then in that workflow, once we've identified them, right, we've got almost this day zero type action that has to happen, right? This is the— right, we gotta go create their logins. For all of us technical people, this is going to be the get them in the HR system, right? This is going to be the offer letter if we've already— haven't already got it signed, right? This is all the pre-hire, as some HR folks would call this. And I don't know if we need to add anything for this conversation, but it's all of this stuff that should just be done beforehand, right? Procure a laptop. You know how many times I would get annoyed at my service manager because the guy would start and I'd go over to their computer and they'd be like, oh, I don't got one.
You know, one of the— and well, we've all had their customer do that to us, right? Hey, a new guy started today. How quickly can you get him a laptop? Right? And we know that they're running around like a chicken with your head cut off that that creates. So let's not do that internally. But, you know, there's some other things too to be thought about, right? When we're putting them in that HR system and Kyle's headed there already, right? The welcome email, but even a welcome packet, right? Especially if you've got folks who are working from home. What's the thing that you can drop in their office, their company polo, some business cards, something just shows up on their, on their, you know, in their home office. That says, hey, you're a member of a new team. Congratulations. Thank you so much. We're looking forward to working with you. That sets an amazing impression right there on day one with somebody we may never meet face to face in this world.
Oh, completely. And that can be demoralizing, right? I know a lot of people love work from home, but that doesn't mean that they don't have pride in where they work. I mean, doesn't mean that they don't want pride in where they work. It's funny. Go ahead.
We hired somebody from a $30 million MSP across town. They were way bigger than us. Um, and when we brought her on, we sent her a nice little swag box and everything. And she spent— this was, this was late 2019, early 2020 when COVID was in full swing. She spent the first 5, 6 months working from home. I never met her for like 6 months. Um, and when I finally met her, she said, you know, I feel like I already know you guys and the culture here has been so great. And that box of stuff you sent me on day one just really moved the needle. And so just think about that. You know, these are things that, that impression lasts beyond the few minutes that it takes them to open that box. They see that little widget or that little swag piece on their desk every day, you know, a business card or whatever. And they remember every single day that, you know, on day one you made them feel wanted.
Mm-hmm. And also there's, you're giving them an air of confidence in that you've done this before, right? And when you are confident, they are gonna feel secure. It's a weird human dynamic to where when you want your employees to be calm and collected and they know they're going to be supported and nurtured, you have to show them that, hey, I know what I'm doing, right? This is like first impressions. This is a second chance at a first impression with that new hire, right? You got to think they had a lot of anxiety trying to fight for the opportunity to work for you, and now it's your turn to return that respect.
And when you may have even gone back and forth and negotiated with them in the beginning, right, you're going back and forth over salary and benefits and whatever, like there may have been a a little stress and animosity while you're bringing this person on. So, you know, this is kind of that reset, like, okay, we've made the deal, we agreed what, what healthy looks like, we agreed what it looks like for you to come to work with me. Now let's set the expectation of what the next 90 days, 180 days, year and a half is going to look like, whatever.
No, exactly. It's within your control. And the one thing that I did at my MSP that actually really made the onboarding process smooth was Day before phone call. Now, I know a lot of times this isn't possible on like a Monday, but, you know, do it on a Friday where just call the employee and say, hey, tomorrow you're starting at 8 AM, right? What's going to happen is you're going to walk in the door, we're going to hand— we're going to go ahead and sit you in an office. Your direct manager is going to be there to communicate with you. We're going to get you a laptop, right? All the stuff that we're going to go over here in a second, but just let them know, like remind them they're not— they're going to forget from the offer letter or the 10 emails you sent them because maybe they're not used to email management. And I want to stick on that one for a second because if you are bringing someone in from a Nordstrom's or a masonry, they've not used email like you have before. They're not used to the calendar management. They're not used to looking at an Outlook calendar. Even though you sent them 365 credentials, they may have not logged in yet and looked at all the email you sent them. And this even happened at Sierra Pacific Group where we were hiring even in other countries. Going, oh crap, I forgot. That's not sometimes how others work. Maybe they were from an MSP and they lived in ConnectWise, right? They literally had the old adage, uh, what was it, Alex?
It's not in ConnectWise, it didn't happen.
Exactly right. So they haven't had a chance to look at a ticket where you outlined everything for them. So just giving them that, here's what you can expect Monday or tomorrow, and then that gets into what happens on day one.. And I, I know a lot of MSPs, they either wing this or they royally fail at this. And, and I think a good way to facilitate this whole conversation on what are the importance— Alex, I think we should do a bad idea session. You want to explain what a bad idea session is?
Yeah, yeah.
So for those of you— yep, go ahead, go ahead. No, go ahead.
So with a bad idea session, what we want to do is get you guys involved in the chat a little bit, right? So 'Let's throw out some things that, that you might— that you think might fit into, into that day one experience.' And with the bad idea session, it's only kind of a joke, right? The premise is that no, there's no such thing as a bad idea. So let's get them all out there on paper. Let's throw these things in and make sure that we understand where we're going and what we're talking about. And then we can kind of parse all the different pieces of the different ideas and organize them into a way that really makes sense.
No, you 100%. This actually came from a Jim Collins interview with the band Aerosmith, and what he had asked them was, hey, how do you guys come up with some of your songs, right? Some of the songs in Aerosmith were kind of weird, like Love in an Elevator, right? Like there's, there's some level of, huh. So the idea is that there's no bad ideas. Anything an employee needs to tackle in their first 60— let's call it 60 days, I think that's an easier time frame than 90 days. Just throw in the chat, what are all the things you want your employees to learn in the first 60 days? And I'm going to— and I'll get some started on here as well. And Alex, you know, feel free to give me some. And we're going to use the Fort framework to help. Now, finance is kind of where I put a lot of HR stuff. So, right, we probably have like I-9s, right? That's a really easy one that everyone in the United States has to tackle, right? We got to make sure I've seen their Social Security card, the birth certificate, they're a citizen. Put it in my HR system and they're ready to go.
And along with this probably goes some sort of HR paperwork, right? What are we asking for from them as far as signing policies, procedures, those kinds of things, right? Hopefully we all have an acceptable use policy and a wire transfer policy and a whole bunch of things baked into an employee handbook. So, you know, handbook docs, those kind of things.
Right. And I think that almost gets its own bullet point here, right? Where is that compliance? Now, what other things, Alex, do you think we have? Like, in my head, right, I'm going from an operational perspective, right? PSA training. How many of us give our team the actual ability to sit there in front of the LMS of our PSAs if they have them and go, hey, how do I put time in, right? I might eventually tell them their timesheet compliance, but I just need to understand the system. Where do I click? PSAs are not a simple tool as much as we try to make it feel like it. Hell, I built an entire company off of a PSA consulting firm, right? Like, this is something that I'm just going to tell you right now, you need to give them time for.
And this isn't just specific to the PSA, right? If you're, if you're using some different tools, if you're somebody who's in a sales role, this is the CRM, right? These are critical line of business applications. Every employee probably lives in 1 or 2 applications and 90% of their day or 95% of their day. So make sure they get training on those. And this is vendor portal stuff, right? Do we go to ConnectWise University? You know, what is it in there that we need them to see? And as we get it in front of them, we just need to think about how we break it out, and we'll get into that in kind of the next step. How do we break it out so that they don't get death by slideshow or death by training presentation so that they have a little bit of sanity left when they're done with this? Because 8 hours a day, you know, 2 weeks in a row of ConnectWise training will get anybody to quit your MSP.
Oh, completely right. Vince is completely right. There is a level to where nobody reads manuals. However, we have to give them the opportunity to read the manual, right? We got to be able to set time aside, right? I think it was you, Alex, that mentioned a, uh, a do not disturb like coffin that they go sit in just to be able to take some of these.
We were talking about this on the side of training, but I think you would use the same, the same concept or the same room, the same facility Right? When, when you send an employee in for training, what's the biggest distraction they have? Well, if it's not their laptop, it's this thing, right? I carry my phone in with me and all my little alerts and bells and whistles and buzzes go off as I'm, as I'm in the room supposed to be doing my training. Same with that onboarding. If I'm supposed to be reading through an employee manual or understanding what I'm signing, we don't want all those distractions. So don't send them in with their personal laptop. Don't send them in with their PC or their, their phone. Give them a place where they can securely stow those. Let them go in and do all this HR stuff on a really generic company piece of equipment that doesn't have a bunch of, a bunch of your corporate or a bunch of your entertainment gadgets on it.
You know what, Alex, you brought something up that I remembered from my MSP while you were talking, which was, right, even though we don't think about it, our MSPs have an internal IT responsibility. So what does that internal IT onboarding feel like for the new employee, right? Where they have the hardware assigned, right? They have the test all the logins, right? Make sure that we did get everything, give them access to everything that they need, right? And maybe just because, right, maybe they are someone from sales or HR or finance and they don't understand technology like us as professionals. Maybe a quick little 365 demo, right? A lot of us use 365 and they need to understand that You don't have to use the web apps. You could use the desktop apps, right? If they're used to it, especially on the finance world, right? They're going to be buried in Excel. And if you just hand them a 365 login, they may be sitting there going, oh, this is BS. Excel Online sucks, right? Because they don't notice that there's a little button that says download the application, right?
Well, and, and there's an opportunity here too to just kind of vet your person and figure out where are they starting, right? What is their, their status quo? Do they have a little bit of knowledge? Do they have some prior experience from somewhere else that they worked? You know, if you know you've got an Excel guru, certainly get those desktop apps installed and make sure that they're in a good place. But this goes for all of your products, right? If somebody spent a decade in ConnectWise as a former employee, you probably don't need to give them the ConnectWise 101. You just need to give them the ConnectWise, hey, how do we do it here? What do we do that you might find different? From a different organization. If they come from Autotask, maybe we've got to start a little further back, right? Same concept, but all the buttons are in the wrong place, right?
And all of these things start to accumulate really to, right, from an operations perspective, which is just job duty, uh, lessons, right? Am I walking them through what a day in the life of this individual works like? If I'm sitting in a Tier 1 seat, right, walking them through, hey, We expect you at 8:05 to be back in your seat and working your first ticket. How will you know you have your first ticket is we will assign it to you right now. I know that sometimes feels a little handholdy, but if you can do this very well, this is where accountability actually becomes a thing because you gave them that time in that first 30 to 60 days to sit down. Here's your training, mister. Here is what I expect of you, which is key to accountability. And I will mentor you to success, right? And I think you really need to go through that with them in the first week, right?
Well, it's about setting that expectation that's going to live for as long as this person is in a relationship with you.
Mm-hmm. Um, here's one that I ran into all the time: payroll. I can't tell you how many employees I hired where I would get a question after like day 4 or 5, or they would look at me and go, So when do I get paid? I don't know if that's just me. Let me know in the comments if that's just, you know, Kyle completely missed a point in my MSP. But it seemed to always be a thing where they were just like, oh wait, you do direct deposit? Oh wait, what is PTO? How do I submit PTO, right? How do I, how do I do all the, uh, PTO slash holiday explanations, right? And I know that goes into HR paperwork, but because this is a bad idea session, I think it gets its own bullet because it's that pivotal to the employee experience.
Well, if you're not doing a good job of calling that out specifically, there are things in your employee handbook you're going to want to highlight, right? And this is one of them, right? Hopefully that is all in there and you can say we get paid on the 1st and the 15th or we get paid every other week or when you're starting in the middle of a pay cycle. So this is what you can expect in your first pay cycle. All that completely spelled out clearly, right? So we want to make sure that we can explain to them what's in the, in that handbook.
Totally. Now, here's one. I did a post on this on LinkedIn the other— it's probably going back a couple months now. Communication expectations. And this one is a little bit— I'm going to put this in ops. I'm going to put communication policy. Now, why do I say that? I don't know about you, Alex. Yeah. How many different ways could you guys communicate with either other employees or with your customers? 71.5.
Whatever it is, there's too many, right? And I had a boss at one point who said, this is how you will communicate with me and this is what I prefer. And while I found that an employee looks at that and thinks, oh, that's helpful, what I realized was that is specific to that boss and does nothing to help align them with the rest of the company. So what I learned from that was Good idea, bad implementation. Proper implementation would be for the company to say, this is how we communicate as an organization. If you're communicating with a customer, everything gets confirmed in a ticket. Even if we have a phone call, we go back into the ticket system and say, to confirm what happened on our call, blah blah blah blah blah. If we're communicating internally, um, and we need action on something, then maybe it also becomes a ticket. Um, if it's not actionable and just informational, maybe it falls into an email. If it's time sensitive, maybe it's a text message or an instant message. But all of that should be spelled out. Like, when do we use email versus when do we use Teams or Slack? And when do we use text messaging? And when do we use Signal, right? And, you know, certain companies have a policy, right? The minute somebody believes there's a breach, hey, we go to something that has disappearing messaging, right? Um, these are all things that, that should be written into your policies. You should understand how these work. And we want to make sure that, that we know exactly, um, and that we're setting the right expectation. And exactly how to communicate with our team.
And I'll— and I want to go one step further on that, just as an aside. If you are an owner on this call and you build a communication policy, you also need to follow that communication policy. And I know it is the most difficult thing in the world, and it will frustrate, frustrate you to no end. However, the second you go around your own policy, your employees are going to notice, and then they're going to—
just made it okay for all of them to do it. Yeah. You just gave them permission.
And I can't tell you how many times I've heard, no one read my email, I sent this long email and no one read it. Well, if every single time you've communicated with them prior has been over Slack or over Teams, right, they're probably not looking at their email. You've never built an expectation for them to look at this email. I used to tell my employees, you check your email once a day. You can pick at the end of the day or at the beginning of your day. After that It should— there should be no reason you go double back on it because I knew as my service employees, 80 to 90% of their day was working with clients, which means it was in the ticket because I— and that actually leads me to one of the other things that we haven't added, which is something I did in my MSP, P&L 101 and how our MSP makes money.
Essentially, how does the P&L impact my job and how does my job impact the P&L?
If you take one thing away from this today, these two things that I personally would cover with every single new hire eliminated any conversation about time entry and documentation.
I literally was having this conversation with a pretty large MSP who reached out to me and said, hey, we're having some troubles in our VCIO process. Would you have a conversation with us? So I hopped on a call with them today. And one of the first things that came up was our VCIOs don't track their time. And we went down the rabbit hole of, do they know how you make money? Well, kind of, maybe, eh? Do they understand that if they don't bill for money, you don't make money and they don't get paid? And so you circle that around pretty quickly and everybody starts to understand it. But if you're not having that conversation, you're just encouraging and allowing that bad behavior.
Yep, completely.
And I know there's— setting this up early.
Well, and there's vulnerability in doing this, right? You as an owner have to be mature enough to have this conversation. But what I found when I started making this expectation was my employees no longer took time entry or documentation as a micromanagement task. They understood that they had inventory, that in order for them to not be overly stressed out and overworked, we had to get a dollar from every single thing we did when it was customer are facing. And I actually did the conversation live at MSP GeekCon, and I did do an example on YouTube. So I'm going to put the link into YouTube. So if you want to see how I gave that conversation, rip it off. Literally take the transcript from that conversation and just give it to your employees. I've made it dead simple for you guys.
So let's, let's shortcut the video and just, just skip to the important parts, right? We're not showing the cut. It's showing the day one employee. Hey, my company made $200,000 last year, right? We're not showing them the actual P&L. We're explaining to them how a P&L works and showing them where they fit into it and how the work that they do enables us to pay everyone else in the organization, keep the doors open, the lights on, and everybody's kids fed and clothed.
Yep, completely. Uh, let's talk about actually a little bit on how we make money because that involves, right, how we're working our help desk for some employees. So, right, we kind of need to be able to show them from an operations— how do managed services work, right? How do— what's the best way we can write this managed services workflow or ticketing workflow? A lot of, um, a lot of employees are going to come in not knowing, right? What is triaging? What is escalations? What's the difference? When a ticket gets assigned to me, am I expected to just start working it? Do I call the customer first? Right. And to— I remember who said it in chat, right? People don't read the manual, right? If you just throw an SOP at them saying, hey, here's a flowchart, they're probably not going to really understand that. So whatever, a lot of this helps. And this is something that's a little bit different, right? Give them time to shadow an employee of their role.
And Vince is calling me out a little here, too, and rightly so. He said, And we mentioned internal communication policies, but we didn't talk about external communication policy. That should be a thing too. If you've got engineers talking to people all day, that needs to be documented, how you communicate with them, what the expectation is, et cetera. He also mentioned acceptable use policies and then CSAT and key security policies and things like that. So certainly some things that we ought to consider there. The conversation around CSAT and NPS and whatever metrics you use for customer success, Um, I used to have a sign hanging on my wall in my office that said, what does winning— how do we know we're winning? And it was just a reminder to my team that, um, sometimes we're not real transparent about what winning looks like, and that's what metrics and KPIs are for. That's what we get from them, right? This is how we keep score. This is how we know that we're winning. We don't come to work every day just to cash a paycheck. We come to work every day to win. And that may be why my MSP was a little tough place to work, but, uh, but we were, we were definitely, uh, focused on what does winning look like?
Well, and that's where if you are hiring someone from another tech company, say enterprise, and they were a sysadmin, it is a completely different culture being in an MSP, right? If I am a sysadmin at a big enterprise, I am an expense category, meaning I just support the revenue-generating staff. So I literally just need to make sure that they are working. My number one KPI is, are my— are the employees of our company fully operational. Let's simplify that. Knock out the tickets as fast as you damn can, and that's all we care about to make sure our systems stay up. But in an MSP, that's not always the number one KPI. Are our customers happy? Do they feel nurtured?
Right?
There's going to be times where you can't fix the problem. However, you can buy yourself a lot of time with some bedside manner, right? I, I had an engineer, tier 3 guy. I gave him a tier 3 role mainly because he literally could make any customer feel like they were being hurt. Yet honestly, he could have fixed half the problems that some of our tier 2 guys could. But the whole office could be on fire, he could walk into the CFO's office and say, we got you, we're gonna fix this. It's gonna burn for a little bit longer, but you know what, just bear with us.
Yep.
And half the time he'd come back with a check and say, hey Kyle, I got a blank check to fix the problem. That has value.
It really does. And, uh, you know, that was, uh, as not the most technical co-founder, that was a superpower that I, that I possess. So, um, you know, it's the, it's the salesman, right? You can send them in there to, to go, to go put on the smiling face, right? Shake hands and, uh, kiss babies and make everybody happy even while the world is falling down. And that is a That's a, that's a tough one to measure, but it is definitely an amazing skill set.
It's tough to measure, but it's easy to see. Yeah, right now, just some other stuff and we'll get off this bad idea session, right? What are your products? What are your services that you offer? Right. Your sales team should be able to spend some time with a new hire saying, hey, here's what we do, here's what our packaging looks like, here's who gets all you can eat, here's who doesn't get all you can eat., right? A lot of times we forget that. And then when we see a request from a procurement side going, hey, can you sell this client a Dell server? You're going to go, but we're an HP shop. But no one ever told them that you're an HP shop, right? So understanding how your product catalog and how your customer success department operates when it comes to these things. Any other last things that you can think of, uh, just to throw on the board?
Yeah, I think that there's also some other things around sales and account management process. If you're hiring a non-technical person, right, they have to understand what those flows look like. At every MSP, those are a little different. So it's not something that we can just come build out for you. But sales and account management process is definitely a big one. There are certain cadences and just different things that we're focused on as we're, as we're going through each of those.
Now, there's one big one that we missed, Alex, and I'm just going to put it here. I don't— we could go down a whole rabbit hole. It could have its own onboarding process. Process in itself.
What about cyber security?
Yeah, phishing training, right? You're not just always hiring nerds. And I hate to say it, I used to phish my own company all the time. The nerds would still click the ones that said your boss is giving you a gift card.
You know, I was talking to Wes Spencer about this one day, and he said, uh, you know, everyone is— everyone is exploitable. You just have to know what the exploit is. And this was back in his, uh, crypto fascination days. And he says, if you sent me a legit-looking crypto email, uh, you know, with the latest crypto news, click here, I probably would click it, especially if I had had a long, busy day and just wanted to kick back and focus on something interesting and exciting to me.
And what's more exciting than the boss giving you an Amazon gift card, right? Right, because everyone does it. Every company just sends them out like as a quick little, hey, employee satisfaction booster. And it's really easy to know who the owner of your company is, right? That doesn't take very long. And at the same time, your sales guys, they're not nerds. Your finance team, they're deaf. I mean, they're nerds, but nowhere near technology, right? It's very much geared towards the numbers so that you need to block time just like you would put on your clients to have those conversations. And why I stumbled there for a second, my brain went, you might be a compliance shop. You might be going after HIPAA clients or FINRA clients or SEC, any CMMC, FT— like, there's so many of them out there now. You may have got a guy that's never dealt in compliance before. He may not know that your customer, before you take a T&M ticket, needs a business document agreement. Now, I would urge you to have processes so that that never hits the guy, but it doesn't hurt for them to know about that, right? At some point, you need to walk them through that. So as you guys can see, there's a lot of things that your employees have to learn in the first 60 to 90 days. And getting back to our agenda a little bit, Alex, what, what kind of like, how do you start? How did you guys start to build out a checklist or a process or a project plan for these employees?
Yeah, it was a, it was a tracking ConnectWise, uh, at my MSP. Really, we did it. We had a period at my MSP where we had a significant amount of turnover, and we were that MSP that hired referrals at this time. We only hired our buddies' buddies. What happens when you only hire your buddies' buddies? Well, when one of them goes and gets a job at the State of Delaware and the State of Delaware says, "Man, you have a great skill set. Who else do you know that knows the kind of stuff you do?" Guess what? Another one leaves and another one leaves.. And we weren't very big at this point. And 3 of my 4 strictly billable engineers rolled out the door within about a 90-day period. So we went from not doing a lot of onboarding because we had really high employee retention to basically re-onboarding an entire team. And that was when we said, oh crap, number 1, our documentation is terrible and we need to improve our documentation. Probably something that should go on our list of things we need to train on, how to do documentation. Oh. And then we also kind of went down the rabbit hole of, well, if we're going to have to bring people in, this is the time. To identify all the things that ought to be in an onboarding plan and start to build that out. So we built it out in the tool that we had and the tool that we used, which was ConnectWise, and Track seemed to kind of make a repeatable, you know, way to rebuild that every time.
And that's exactly how we did it because we recognized that there would be these phases of an employee. But at the same time, right, we wanted some logic, we wanted a calendar, we wanted to be able to block time for them to take certain sessions. Everyone knew that if they didn't put it on my calendar, I would not do the session with the employee. They just had to put it on there because I'm such a calendar-driven individual. So they, they did have to also though have a completion side, right? That trust and verify. So what Alex and I have done for you guys is part of the worksheet that we're going to show you and we're going to give you all here in a minute is we do have the ability to start tracking our phases and our tasks, right? So we kind of talked about like Oh, it's a horrible color. Let's do— let's try black or red. Let's try red. Oh, that's better, right? Our HR stuff, right? It's due on week 1, right? And the due date would be, right, whatever. And then the completion date, which would be what the service manager or the manager of that employee would need to turn in to say, hey, this employee's onboarding is completed, right? So this is that trust and verify where they can then go Hey, I got you. And this is a critical step because a lot of you may go, well, I'm hiring this guy after it's needed, right? After they are needed. So I can't just sit them at a desk learning. They need to be productive. And this goes into that, that pulling the string from both ends logic of, well, they still need to get it done at some point. So while you may not have a full-blown 12 weeks of training that you can afford your employee to do, you owe it to them to stretch it out over a time period that they can afford to get all of these things done.
Yeah, have you ever put an employee in front of like 8 hours of ConnectWise training in a day? Some folks are— some folks— so did we, and some folks were kind enough not to scream at us, but, uh, what we found was they retained zero. Right? It was just this— they're drinking from the fire hose for hours and hours and hours. It's not exciting. It's not engaging. It doesn't get you interacting with it. So you have to give them breaks in between and give them other things to go do and let them go hang out in the service desk and ask questions and, you know, interact with people and do those kind of things along the way. So that's why, as we look at this, we're looking at, you know, 6 weeks, 8 weeks, 12 weeks as we break some of this training out, even if it's only 40 or 50 hours of training. We're going to break it out over a really long period of time so that we get them up to speed consistently and at a good pace, but also that we don't get them to a point where they just pay attention to nothing and click, you know, kind of checkbox compliance, go next, next, next through all the trainings and just get it done as quick as they can because they can't stand to spend one more hour in that training.
No, exactly. And that's where, right, don't be afraid of checkmark type training. What do I mean by that? Right, let's say that I want them to shadow a like role for an hour. So, right, I just want shadow for 1 hour. Now, when I say the word shadow, if you've never heard that before, that's just I want to go sit side by side with someone that has the exact same role with me and just watch them work. Now, be strategic in who they shadow, right? Don't put them on that guy that doesn't like doing time entry. But right, that shadow for 1 hour, right, that could be during week 1, and then I might have it again, right, down here in week 2 because Like you mentioned, Alex, I can't sit in front of ConnectWise training for 8 hours. So how do I break up that day into two parts? Now, if you got as neurotic as I did, my employees actually had their first 60 days, mornings and afternoons, 100% laid out. What do they do in the morning? What do they do in the afternoon? Now, financially, I built my model to where all of our employees were being hired pretty much a month before. And when I say a month before, like they started 30 days before they were needed. So I understood that first 30 days I didn't have to see them being billable. I just completely wrote off their salary in that first month. Now, in doing that, they have to have it all done by day 30, right? It was a sprint. So in that, right, you mentioned Alex, right? Not everyone does it the same way. Right? That's where I understood that day 31, they may ask questions about day 2 because they have forgotten it by that point. So we had to have a mentor system day 31 through 60 of just reminder training sessions, right? Like, go quiz them, go challenge them, go mentor. Or rather than a shadow of me watching somebody do it, have the person that they were watching watch them do it, right? Reverse the roles. And that becomes extremely successful because Rather than them making a mistake, someone is guiding them to success.
Yep, absolutely.
Right? It's Luke being— it's having Obi-Wan talking Luke's ear on, right? You don't need to use the guidance system, right? Just feel it.
And there's a lot to be said for that, right? And especially when you're new at a job and it's nice to be able to think you did something and then just have somebody go look at it and say, did I get that quite right? Right. This is, is this what you meant when I heard you say this? There's a lot of value to be able to just go back and say, sanity check me here. And there goes my camera being ridiculous.
Yeah, it happens. So for all of you that are in chat, right, what we are— and, you know, a lot of you are probably even going right now of like, man, they've listed out a bunch of things. So I do want to show everybody what we have actually as a giveaway today. Which is our official onboarding document. So I don't know if you want to walk them through this a little bit, Alex.
Yeah, might as well take a couple minutes as we kind of scroll through here. You know, really what we're looking at for our— for the opportunity, and there's some instructions here on how to fill it out. But what we're talking about is take a few minutes, go through this, and start to fill in the things that you expect your employees to do within the time frame that they're expected to do it in. So, you know, if you expect every employee to do the same thing on day 1, day 3, day 5, day 7, get those things documented here. This may change by job role, and that's okay, but you may fill this out a couple different times, a couple different ways depending on who's in what job role. And as we work our way down, you'll see those, you know, are we doing this in week 1, are we doing this in week 2 or week 3? You may have 10 things they do on week 1, right? It may be day 1 morning, day 1 afternoon, like Kyle was talking about, or it may be 3 things on day 1. Strictly shadowing on day 2 and back to the classroom on day 3. Just kind of depends on how your MSP is built. And, you know, we always had things throw us for a loop. We'd send an engineer out to shadow somebody and we thought they'd be gone for 2 hours, and typical to MSP, they're gone all day, and that breaks their training plan, right? So, but as we go down here, reprint this page as many times as you need it to be able to go back through and create the full 30 or 60 or 90-day onboarding plan, whatever it is that you're building. And then the last couple of pages— did we keep the notes pages in there, Kyle? So yeah. So there's some pages down here at the bottom that give you visibility into just some ideas. These are, these are the bad ideas that we threw together to say, hey, here's a bunch of things that ought to spur your, your thought processes about, about what you could and should train your folks on as you go. There's about 4 pages of those, I think. Yeah. And, and those will help you to generate something that's usable by your MSP. To show folks what, what onboarding really looks like or what good looks like. Right? How do we know we're winning? Well, you know, we're winning if we can get through this in 30 days or 60 days or 90 days and our employees start to come out of the chute a little bit more standardized, a little bit more ready to go to work and with a better understanding of what it is we do.
Well, and beyond that, this is an iterative, improved process. Don't think you are going to get straight to best-in-class employee onboarding on day one, because when you put together that first project plan, as you mentioned, Alex, we did the same thing. We had project templates that we would deploy for every new employee. So it immediately had all of the tickets that we would assign the employees. We would always go back at the end of every new hire and say, employee feedback, hey, tell us how we did on onboarding. What things did you wish you knew? And we would do it at day 90 and day 6 months or whatever that is, 180. And why we did that was what frustrated you? What did you wish you knew? And they would tell us, right? They would say, man, you never told me really how to do the timesheet accurately. You never really went into projects with us. You never went into kind of client communication standards and how I should phrase my ticket note resolution, right? You're going, oh shit, I forgot about that. And we'd go back over.
Nobody ever told me not to type clear text passwords into the, into the PSA until somebody yelled at me about having an admitted ticket, right? Those things all happen the way we would phrase that at my MSP. And we would always have these regular check-ins, right? If you're training somebody like this, you're probably having daily check-ins and weekly check-ins. Every week we would ask them, how'd your week go? And what could we have done better or different to prepare you for this week?
Mm-hmm.
Right? That's a phrase you'll hear me use all the time. What could we do better or different? Because it's not like they feel like now I'm asking them to tell me how bad I suck. I'm just asking for some feedback that would— and people, I find people are more open to providing a little feedback if it's not phrased negatively, right? So what could I have done better? They'll give you a little coaching and a little guidance. We did that every single week up until they had been with us for about 3 months.
And this is what will stretch your onboarding process to, to be 60 days, 90 days, 120 days. And then you start to ask the question of, is this onboarding or is this training? And when you ask—
there's a point which it converts.
That's beautiful. Right.
Point at which your daily check-ins turn into weekly check-ins and you're, you know, all these things start to spread out and stretch out. And for every MSP, that's different. For us at my MSP, 3 years ago, that was about 90 days. About 90 days we would convert to weekly check-ins. But then those weekly check-ins give us the opportunity to say, hey, you know, what are you— what are you feeling like your strengths and weaknesses are? Where did you get stuck this week? What was the thing we could have done to set you up for better success this week? And we never stop asking that question.
It's really the employee QBR, right? It turns into a quarterly check-in of what is that employee path intent, right, where we are going to get to a place where we can get you to your career goals, right? They may be a greenhorn, but they have 4 kids., and they need to go, hey, I know you're paying me for a Tier 1 salary and I'm making $20 an hour, but I really want to get to $50 an hour, $40 an hour. Now, rather than strong-arming them, right, you need to have a professional conversation of, right, that might take a few years, right, for us to grow. But if you support us growing and you tackle out this career path, the second one opens up, it won't even be a conversation who gets it. I know who gets it. So that's how it works.
So powerful, right? Having had those conversations with your employees ahead of time, and I'll encourage you all to really go have those conversations. If you think you've kind of almost had that conversation, your employee doesn't realize you had it. If it wasn't documented and it's not reviewed regularly, your employee has a different understanding of where they're at in that career path than you do. So just make sure you realize this is no different than client communication. If you think you're kind of almost there, you're not even close. And it's time to go have that conversation again and again. It's like being a parent. You have to say the same thing 18 times before they hear it once. So make sure this stuff is documented. Make sure that you're putting this stuff in front of them in a fashion that you can review it and update it and touch on it on the regular, because these are the things that create employees who love where they work and want to stay there longer.
Mm-hmm. And eventually you'll get to a point where you say, hey, how can we reduce the time in the onboarding experience? How can we get them to productivity faster? How do I get an ROI for my employee quicker, right? That's where you're now thinking in an economy of scale model of I need to reduce the investment by either having better training, right? Is there a tool or is there a platform that I can utilize to have this make it a little bit more efficient, right? Not just tickets in ConnectWise, but are there videos that they can go watch? Are there tests that they can go take? Are there labs that they can go play with things in. So rather than watching, can they go break someone's computer 20 times because it's in a lab and I don't care, right? There's where you start to get speed to onboarding, which becomes kind of the next level of maturity.
Meg threw a great question or a great comment in chat. We should, we should share this. She said we always ask new hires to share their oh shit moment. Basically what we say is that at some point when you start with a new organization, you're going to have the thought like, did I make the right decision? Am I in the wrong place? And we ask our new hires up front to share that with us as soon as possible, like the minute it happens. And this way it's super eye-opening for them and it helps them grow the relationship with the new hire immediately. To me, it says, Kyle, I'm hiring you and I trust that you're not going to panic on me, but I also trust that you'll raise the red flag when there's a level of discomfort. And that would help me. It would be valuable to me. And now I'm getting a little, a little vulnerable with Kyle, right, and saying, hey, we're gonna screw up at some point, right? So why don't you just agree to tell me when it happens and know that I won't be upset with you for it, and we can move on through that. So that's great feedback, Meg. I appreciate that. Everybody's gonna like that comment.
Well, and how beautiful is that when I'm a new employee and my boss sees something I did wrong, or I did something wrong, and they understand, or they are able to have a conversation without browbeating me, without holding me accountable, where Right? I can be vulnerable enough to my company and say, I don't know if I can achieve this right now. I need more. Right? So many employees do poor work because they're afraid to tell you they don't have the skills.
I didn't go down— I don't want to go down this rabbit hole because it'll take us way too long. But the book Extreme Ownership, if you're— if your new employees are failing you, the book Extreme Ownership will help guide you towards how to solve for that. So Jocko Willink, great book. Um, all right, so what's left, Kyle?
We're looking at some housekeeping, guys. RejectionCon— this is our pay-what-you-can model for your MSP. All those great talks— you've heard us talk about it 100 times, you've probably seen it on LinkedIn about 47 times at this point in the last week, uh, but really what this is, is all those talks are great MSP thought leaders and operational expertise that you probably don't hear from very often because the industry sometimes rejects their talks because they're not paying money. I said it. So we wanted to give a platform that would go to charity. So 100% of the proceeds go to the Rural Tech Fund. It's a fantastic cause. Just pay what you can, hop in, and it's going to be in Crowdcast. So all of the sessions will always be viewable offline for everyone that does participate. There's also an MSP pass where your entire MSP can go and attend. So please, please, please go ahead and get your tickets. It's 100% virtual. There's no plane flights. Literally, if we're talking about employee education, they're probably going to learn something from this, even if they're not directly involved. I remember one time I sent one of my employees to IT Nation Connect and they sat in on a couple sales calls and they're an engineer. And in those conversations that they listened to, they came up to me and said, hey, boss, we have a problem with our MSP package. And I literally sat there kind of dumbstruck for a second going, holy crap. I would have never thought I would have heard those words out of your mouth. So it's those types of things. Just learning through osmosis goes a long way.
Agreed.
Other than that, guys, we're at time. So I want to respect everybody, right? Join us on the 19th. We're going to go through sales commission planning. So go ahead and mark your calendars. We'll go ahead and put a calendar invite in the follow-up newsletter. I do have the link for the form inside the Crowdcast chat. So if you're watching this down the road and you're going, Hey, where did Kyle put that? It's in the chat inside of Crowdcast. So all of our links will be in there from now forward. Other than that, it's been fun.
Thanks everybody for hanging out.










